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Patented Oct. 22, 1946 '
2,409,883
UNITED STATES PATENT OFFICE
2,409,883
RESINOUS DIBASIC GARBOXYLIC ACID
SALTS OF A GUANIDINE AS
MOTHPROOFERS
.
Vartkes Migrdichian, Greenwich, Conn.,‘assignor
to American Cyanamid Company, New York,
N. Y., a corporation of Maine
-
No Drawing. Application February?, 1940,
Serial No. 317,173
13 Claims. (01. 167-37)
1
The present invention relates to salts of dibasic
carboxylic acids containing a guanidine group,
which are resinous or non-crystalline in charac
- ter, useful as mothprooflng agents.
There'is on the market today, a mothproofing
composition, the active ingredient of which is di
xylyl guanidine oleate dissolved in petroleum
naphtha. The fact that cloth treated with a
heavy dose of the above composition acquires a
greasy feel is objectionable. .
‘
vThe principal object of the preesnt invention,
_ therefore, is to provide a guanidine or substi
2
whereupon combination to the salt takes place al
most . instantaneously.
.
Still another method which avoids the necessity _ ,
of evaporating off large quantities of alcohol, is
to dissolve a small portion of the mixture of the
acid and free or substituted guanidine in warm~
. alcohol and adding more of the mixture while the
liquid is kept-hot. Proceeding in this manner
and starting with a comparatively small quantity
10 of alcohol, any amount of the corresponding salt containing the guanidine group may be prepared.
The small amount of alcohol in the ?nal product
is not objectionable and may be eliminated if so
tuted guanidine salt suitably soluble for applica
tion to fabric which will effectively protect such
desired by grinding the chilled product and dry
cloth against the ravages of the carpet beetle 15 ing in the usual manner.
_
and/0r webbing clothes moth larvae without
These compounds are not soluble to any great
taking on this objectionable feel, even in heavy
extent in petroleum fractions but are to a limited
dosages.
extent in chlorinated hydrocarbons and in arc
It has been discovered that salts of guanidines
matic hydrocarbons. They are quite soluble in
' or substituted guanidines may be obtained by re 20 . alcohol. The solubility of these compounds in
acting the free guanidine or substituted guani
petroleum hydrocarbons may be increased by the
dine with dibasic carboxylic acids. A large num
addition of alcohol. To the alcoholic solutions
_ber of these compounds have been prepared and
thereof, large proportions of carbon tetrachloride v
the very remarkable discovery made that all of
may be added without causing precipitation. The
these salts, with the exception of the oxalate, are 25 addition of this last substance to their alcoholic
of a resinous character. This is a desirable char
solutions to a large degree eliminates the ‘fire
acteristic in a substance used for mothproo?ng
hazard attendant upon the use of alcohol alone.
in that it has a tendency to adhere to the fabric
From 1 to 5% of the guanidine compound may
when deposited thereon from its solutions. In the
be readily dissolved in an ethyl alcohol-carbon
case of crystalline material such as the oxalate, 30 tetrachloride mixture containing 10% of the al
the deposited crystals of the salt may be brushed
cohol. ' Such solutions may be sprayed on the
or rubbed therefrom with consequent loss of
cloth at the rate of one gallon to from ten to
mothproo?ng characteristics.
thirty pounds of cloth, or the cloth may be dipped
While the dixylyl guanidine salt of a dibasic
in the solution, wrung out and then dried‘. '
carboxylic acid is preferred, yet other mono or 35 A medium weight white wool ?annel, a brown
poly substituted guanidine salts thereof are use
wool cloth and a woolen suiting were used .in a
ful, such as those of the alkyl, arid and alkyl aryl
series of tests with salts of the above acids con
groups, as well as the unsubstituted guanidine
taining a. guanidine group, with the exception of
salts. Any dibasic carboxylic acid except oxalic
the oxalate, which was unsuitable because of its
may be used, such as malonic, succinic, glutaric, 40 crystalline nature. The compounds were ap
plied in solution in a mixed alcohol-carbon tetra
adipic, pimelic, suberic, azelaic, sebacic or the like.
chloride solvent at various rates and the re
These compounds may be readily prepared by
sistance of the treated pieces to the attack ‘of
dissolving the acid in alcohol, adding the equiva
lent quantity of the free guanidine or substituted 45 black carpet beetle and webbing clothes moth
larvae tested. -All solutions contained a quan
guanidine and evaporating oi the excess alcohol.
tity of the guanidine salt equivalent to approxi
They may also be made by adding equivalent
mately 3%. All samples of cloth which had had
quantities of the guanidine or guanidine com
an application equivalent to as much as one
pound to the molten acid.
gallon
per ten pounds of cloth had complete
These guanidine and substituted guanidine 60 protection.
This resistance to destruction by the
salts are fusible, so that an alternative convenient
above insects was ineffective only when the ap
method of preparing them is to add a mixture in
plication dropped to one-third of a gallon per
equivalent quantities of the acid and the free
ten pounds of cloth. '
cuanidine or substituted s'uanidine to the fused
Many of the above substances are new chem
guanidine salt, heating until all solid disappears,
ical compounds.
-
'
2,409,883
3
4
.
substituted guanidinesalt of a dibasic carboxylic
acid, the salt having resinous properties.
‘ While the invention has been described with
particular reference to speci?c embodiments, it
is to be understood that it is not to be limited
thereto but is to be construedbroadly and re
stricted soley by the scope of the appendedclaims;
I claim:
.
g
'
1. A mothproo?ng composition containing a
dixylyl guanidine sebacate, the salt having resins
ous properties.
2. A mothproo?ng composition containing a
dixylyl guanidine‘salt- of malonic acid, the salt
having resinous properties.
'
3. )A mothproo?ng composition containing a
dixylyl guanidine salt of succinic acid, the salt
having resinous properties.
_
'
.
'
-
5. A method of mothproo?ng which includes
the step of contacting the material to be moth
proofed with a composition containing-a substi
tuted guanidine salt of a dibasic carboxylic acid,
the salt having resinous properties.
guanidine sebacate, the salt having resinous
properties.
'10. A method of mothproo?ng which includes
the step of contacting the material to be moth
15 proofed with a composition containing, a guan- '
4
4. A method of mothproo?ng which includes
the step of contacting the material to be moth
prooi’ed with a composition containing a guan
idine salt of a dibasic carboxylic acid, the salt
having resinous properties.
t
, 8. A method of mothproo?ng which includes
'. the step of contacting the material to be moth
5 proofed with a composition containing a dixylyl
guanidine salt of a dibasic carboxyiic acid, the
salt having resinous properties.
9. A method of mothproo?ng which includes
the step of contacting the material to be moth
proofed with a composition containing a dixylyl
7
6. A method of mothproo?ng which includes
the step of contacting the material to be moth
idine salt of malonic acid, the salt having resin
ous properties.
‘
.
11. A method of mothproo?ng which includes
the step oi? contacting the material to be moth
20 proofed with a composition containing a dixylyl
guanidine salt of malonic acid. the salt having
resinous properties.
12. A method of mothproo?ng which includes
the step of contacting the material to be moth
25 proofed with a composition containing a guan
idine salt of succinic acid, the salt having resin
ous properties.
13. A method of mothproo?ng which includes
stituted guanidine salt of a dibasic carboxylic
the step of contacting the material to be moth
acid, the salt having resinous properties.
30 proofed with a composition containing a dixylyl
7. A method of mothproo?ng which includes
guam'dine salt of succinic acid, the salt having
the step of‘ contacting the material to be moth
resinous properties.
proofed with a composition containing a diaryl
,
VARTKES MIGRDICHIAN. ,
. proofed with a composition containing a, disub
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